IP Library Granted Patent US 10,370,570
Granted Patent B2
US 10,370,570 · App. 14/741,758 · Granted Aug 6, 2019

Low-modulus silylated polyurethanes

Inventors: Lars Zander (Altoetting, DE); Helmut Loth (Haan, DE); Marc Pascal Burmeister (Duesseldorf, DE); Rolf Tenhaef (Duesseldorf, DE); Johann Klein (Duesseldorf, DE); Jan-Erik Damke (Duesseldorf, DE)
Assignee: Henkel AG & Co. KGaA
C09J175/08C08G18/0852C08G18/10C08G18/12C08K5/0016C09K3/1021C08J2375/08
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 10,370,570
App. No.
14/741,758
Granted
Aug 6, 2019
Kind
B2
Abstract

A method for producing a silylated polyurethane that comprises the following steps: (1) reacting at least one polyether polyol having a number average molecular weight of at least 2,000 g/mol with at least one polyisocyanate in the presence of at least one solvent; (2) reacting the reaction product of step (1) with at least one silane of formula (I) A-R—SiXYZ (I), where A means —NH 2 or —NHB, wherein B stands for a branched or linear alkyl radical with 1-12 C atoms, possibly having functional groups, a cyclic alkyl radical having 5-8 C atoms, or an aryl radical, R is a divalent hydrocarbon radical having 1-12 C atoms, and X, Y, Z are substituents on the Si atom and are independently of each other C 1 -C 8 alkyl, C 1 -C 8 alkoxy or C 1 -C 8 acyloxy groups, wherein at least one of radicals X, Y, Z is a C 1 -C 8 alkoxy or C 1 -C 8 acyloxy group, in the presence of at least one solvent. Further disclosed is a silylated polyurethane that can be produced by the method, a curable composition based thereon, and the use of such a composition as an adhesive, sealant and/or coating material.

Claims (27)

1. Method for producing a silylated polyurethane, comprising the following steps:

(1) mixing at least one polyether polyol having a number average molecular weight of 10,000 to 16,000 g/mol with at least one polyisocyanate and at least one solvent;

(2) reacting the at least one polyether polyol having a number average molecular weight of 10,000 to 16,000 g/mol with the at least one polyisocyanate in the presence of the at least one solvent to form a reaction product, wherein the solvent includes an aromatic compound comprising a C 10 -C 20 alkyl group;

(3) reacting the reaction product from step (2) with at least one silane of formula (I)

A-R—SiXYZ  (I),

wherein A means —NH 2 or —NHB, where B stands for a branched or linear alkyl radical which contains 1-12 C atoms and optionally functional groups, or stands for a cyclic alkyl radical containing 5-8 C atoms, or an aryl radical, and

R is a divalent hydrocarbon radical containing 1-12 C atoms, and

X, Y, Z are substituents on the Si atom and independently stand for C 1 -C 8 alkyl, C 1 -C 8 alkoxy, or C 1 -C 8 acyloxy groups, at least one of the radicals X, Y, Z standing for a C 1 -C 8 alkoxy or C 1 -C 8 acyloxy group,

in the presence of at least one solvent, wherein the solvent includes an aromatic compound comprising a C 10 -C 20 alkyl group.

2. Method according to claim 1 , wherein the solvent is a C 10 -C 20 alkyl-substituted benzene.

3. Method according to claim 1 , wherein R in formula (I) is a methylene, ethylene, or n-propylene group.

4. A curable composition consisting of the following components in the corresponding weight fractions:

10-40% by weight of silylated polyurethane produced by

(1) reacting at least one polyether polyol having a number average molecular weight of at least 2,000 g/mol with at least one polyisocyanate in the presence of at least one solvent, wherein the solvent includes an aromatic compound comprising a C 10 -C 20 alkyl group;

(2) reacting the reaction product from step (1) with at least one silane of formula (I)

A-R—SiXYZ  (I),

wherein A means —NH 2 or —NHB, where B stands for a branched or linear alkyl radical which contains 1-12 C atoms and optionally functional groups, or stands for a cyclic alkyl radical containing 5-8 C atoms, or an aryl radical, and

R is a divalent hydrocarbon radical containing 1-12 C atoms, and

X, Y, Z are substituents on the Si atom and independently stand for C 1 -C 8 alkyl, C 1 -C 8 alkoxy, or C 1 -C 8 acyloxy groups, at least two of the radicals X, Y, Z standing for a C 1 -C 8 alkoxy or C 1 -C 8 acyloxy group, in the presence of at least one solvent, wherein the solvent includes an aromatic compound comprising a C 10 -C 20 alkyl group;

10-30% by weight solvent

10-80% by weight filler

0.01-1% by weight curing catalyst

0-10% by weight auxiliary substances

where the weight fractions add up to 100% by weight, and are based on the total weight of the curable composition.

5. A curable composition according to claim 4 , wherein the polyether polyol has a number average molecular weight of 7,000 g/mol to 16,000 g/mol.

6. A curable composition according to claim 4 , wherein the filler is calcium carbonate.

7. The curable composition of claim 4 being an adhesive, sealant, and/or coating.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 11, 2016
From: ZANDER, LARS; LOTH, HELMUT; BURMEISTER, MARC PASCAL; TENHAEF, ROLF; KLEIN, JOHANN; DAMKE, JAN-ERIK
To: HENKEL AG & CO. KGAA
Reel/Frame 039400/0313 →
Priority Claims (1)
DE 10 2012 223 422 · Dec 17, 2012 · national
Continuity (2)
Continuation PCTEP2013076582 · Dec 13, 2013
Related Publication 20150284610A1 · Oct 8, 2015